LU84295A1 - PROCESS FOR THE PREPARATION OF PHENOXYBENZOIC ACIDS - Google Patents

PROCESS FOR THE PREPARATION OF PHENOXYBENZOIC ACIDS Download PDF

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LU84295A1
LU84295A1 LU84295A LU84295A LU84295A1 LU 84295 A1 LU84295 A1 LU 84295A1 LU 84295 A LU84295 A LU 84295A LU 84295 A LU84295 A LU 84295A LU 84295 A1 LU84295 A1 LU 84295A1
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Luxembourg
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atoms
formula
group
temperature
eue
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LU84295A
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French (fr)
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El-Ahmadi I Heiba
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Rhone Poulenc Agrochimie
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Publication of LU84295A1 publication Critical patent/LU84295A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N1/00—Preservation of bodies of humans or animals, or parts thereof
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    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
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    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
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    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
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    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
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    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C311/52—Y being a hetero atom
    • C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
    • C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/60—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
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    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
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    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • C07C319/12—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by reactions not involving the formation of mercapto groups
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    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
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    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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    • C07C323/36—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group the sulfur atom of the sulfide group being further bound to an acyclic carbon atom
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    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic System
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic System
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/141—Esters of phosphorous acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
    • C07F9/40—Esters thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Description

La présente invention concerne un procécé perfectionné ce préparation ce certains cérivés c'acices phénoxy-benzoïques à croupe sulfcnamic.e ayant ces propriétés herbi-cices.The present invention relates to a process improved this preparation certain cerives c'acices phenoxy-benzoic rump sulfcnamic.e having these herbic-cices properties.

5 Des cérivés hercicices c'acïres phéncxybenzoioues è groupe sulfonsmioe sont connus es ns les cernantes ce brevets européens 3£it et 23352.5 Hercice cerives such as phenoxybenzoioues with a sulfonsmioe group are known from the European patents 3 £ it and 23352.

Ces cemances ce brevets civuiguent ces produits ce formule : luThese cemances this patents certify these products this formula: read

C ,B RC, B R

y-/ _/ 0 Vy s (I)y- / _ / 0 Vy s (I)

E ' X FE 'X F

13 et leurs sels, dans laquelle : A est 1’hycroçère, le fluor, le chlore, le brome, l'ioce, un groupe nitre; -K-NCF, ; PCLH et <ses esters c'sl-13 and their salts, in which: A is the hypercer, fluorine, chlorine, bromine, ioce, a nitre group; -K-NCF,; PCLH and <its esters c'sl-

S ZS Z

2C kyle ce 1 à A atomes de carbone ; N FU, NHOH, N* ; un -groupe csrbcxyle ou l'un ce ses cérivés fonctionnels ; un groupe monoou cislkylaminc ; un groupe NH-CD-R·*" dans le- l quel R est ur, radical alkyle ou alkoxyle ou moncslkyls-mino ou cialkyiamino ; un groupe alkyle ; trialkylammonio, 25 NHS0,.Rz où r. est un racical alkyle ou phényle ; L· r r* NHCLkt-.Sü^n , où h*· a la signification céjà indiquée, sikylthio, alkylsulfinyie, alkyisuifenyie, cielkylsul-fonio, cyancsulfonyle, hycroxy, alkanoyloxy, alkoxy, alkoxy substitué pai un slkoxycerbcnyle, SH, nitrcsc, -SCN, szide, 3u CF-., -N=!«-P- ( CCH-. ), scyle ;2C kyle ce 1 to A carbon atoms; N FU, NHOH, N *; a csrbcxyle group or one of its functional cerives; a mono or cislkylaminc group; an NH-CD-R · * "group in which R is ur, alkyl or alkoxyl or moncslkyls-mino or cialkyiamino group; an alkyl group; trialkylammonio, NHS0, .Rz where r. is an alkyl or phenyl radical ; L · rr * NHCLkt-.Sü ^ n, where h * · has the meaning already indicated, sikylthio, alkylsulfinyie, alkyisuifenyie, cielkylsul-fonio, cyancsulfonyle, hycroxy, alkanoyloxy, alkoxy, alkoxy substituted by a slkoxycerbcscyl, SH -SCN, szide, 3u CF-., -N =! "- P- (CCH-.), Scyle;

Iu· 4, n zIu4, n z

OO

c est i ' hycrccèr.e, le fluci, le chlcre, le trcr.e, l'ioce, ou un çrcupe alkyle, aikcxy, alkylsuifinyle, ai- / kylsuifcnyie, C.*·-, LL,,, CL, Nh0, LHCCr.“ eu F- est si/ 35 céfini ccrr.re ci-cessus eu CGNH, ; /j// I ' f 2 C est l'hydrogène ou un halogène ou un groupe al-kyle ou dialkylami.no D est le fluor, le chlore, le brome, l'iode ; ou un groupe CF^, alkylthio, alkylsulfinyle, alkylsulfonyle, 5 halogenoalkyle, sulfamoyle, formyle, alkylcarbonyle, CN ou diméthylamino ; E est l'hydrogène ou un groupe halogenoalkyle, al- koxy, alkylsulfinyle, alkylsulfonyle, CN, CF,, NH0,c is i 'hycrccèr.e, fluci, chlcre, trcr.e, ioce, or an çrcupe alkyl, aikcxy, alkylsuifinyle, ai- / kylsuifcnyie, C. * · -, LL ,,, CL, Nh0 , LHCCr. “Eu F- si si / 35 céfini ccrr.re above eu CGNH,; / j // I 'f 2 C is hydrogen or halogen or an al-kyle or dialkylami.no group D is fluorine, chlorine, bromine, iodine; or CF ^, alkylthio, alkylsulfinyl, alkylsulfonyl, halogenoalkyl, sulfamoyl, formyl, alkylcarbonyl, CN or dimethylamino; E is hydrogen or haloalkyl, alkoxy, alkylsulfinyl, alkylsulfonyl, CN, CF ,, NH0,

Il -5 ^ C0NH2, NH-CO-R , R ayant la signification déjà in- 10 diquée ;Il -5 ^ CONH2, NH-CO-R, R having the meaning already indicated;

F a l'une des significations données pour BF has one of the meanings given for B

R est un groupe -C0N(R^)S09R3 dans lequel , 4 x * R est l'hydrogene ou un groupe alkyle de 1 à 4 I atomes de carbone E 3 15 R est un groupe phényle, pyridyle ou thiényle éventuellement substitué par un ou plusieurs atomes d'halogène, ou groupes alkyle, ou groupes nitro ; ou un radical alkényle ou alkynyle ayant 2 à 4 atomes de carbone ou un radical alkyle de 1 à 4 atomes de carbone éventuellement * > 20 substitue par un ou plusieurs atomes de fluor, chlore, brome ou iode, de préférence CF^, ou par un ou plusieurs des substituants suivants : carboxyle, alkoxycarbonyle de 2 à 5 atomes de carbone, alkylcarbonyle de 2 à 5 atomes de „ carbone, mono ou dialkylcarbamoyle dans lequel les groupes 25 alkyle ont de 1 à 4 atomes de carbone, alkylthio, alkylsulfinyle, alkylsulfonyle, chacun ayant de 1 à 4 atomes de carbone, alkylcarbonyloxyle de 2 à 5 atomes de carbone, al-kylcarbonylamino de 2 à 5 atomes de carbone, ou cyano.R is a group -C0N (R ^) S09R3 in which, 4 x * R is hydrogen or an alkyl group of 1 to 4 carbon atoms E 3 15 R is a phenyl, pyridyl or thienyl group optionally substituted by a or more halogen atoms, or alkyl groups, or nitro groups; or an alkenyl or alkynyl radical having 2 to 4 carbon atoms or an alkyl radical of 1 to 4 carbon atoms optionally *> 20 substituted by one or more atoms of fluorine, chlorine, bromine or iodine, preferably CF ^, or by one or more of the following substituents: carboxyl, alkoxycarbonyl of 2 to 5 carbon atoms, alkylcarbonyl of 2 to 5 carbon atoms, mono or dialkylcarbamoyl in which the alkyl groups have from 1 to 4 carbon atoms, alkylthio, alkylsulfinyl, alkylsulfonyl, each having from 1 to 4 carbon atoms, alkylcarbonyloxyl from 2 to 5 carbon atoms, al-kylcarbonylamino from 2 to 5 carbon atoms, or cyano.

Selon les procéoés connus, les produits de formule 30 (I) peuvent être préparés par réaction entre 25 et 140°CAccording to known processes, the products of formula 30 (I) can be prepared by reaction between 25 and 140 ° C.

d'un halogènure d'scioe intermédiaire de formule : c_ys> _^COX / d-: fVow fr~A (II) Π/ 35 yJ -V (f E F / » 3 dans laquelle X est le chlore, le brome ou l'iode, et A, B, C, D, E, F ont les significations déjà indiquées, avec un sulfonamide de formule : 5 R3Sû2NH2 (III) où R3 a la signification déjà indiquée, en présence d'un accepteur d'acide, notamment une amine tertiaire telle que la Ni,h-diméthylaniline ou la pyridine, ou un carbonate de métal alcalin tel que le carbonate de potassium anhydre, ou 10 un fluorure de métal alcalin tel que le fluorure de césium.of an intermediate scioe halide of formula: c_ys> _ ^ COX / d-: fVow fr ~ A (II) Π / 35 yJ -V (f EF / »3 in which X is chlorine, bromine or l 'iodine, and A, B, C, D, E, F have the meanings already indicated, with a sulfonamide of formula: 5 R3Sû2NH2 (III) where R3 has the meaning already indicated, in the presence of an acid acceptor, especially a tertiary amine such as Ni, h-dimethylaniline or pyridine, or an alkali metal carbonate such as anhydrous potassium carbonate, or an alkali metal fluoride such as cesium fluoride.

Les composés de formule (I) dans laquelle R^ est l'atome d'hydrogène peuvent être alkylés de manière connue, par exemple par réaction d'un diazoalcane de 1 à 4 atomes de carbone, de manière à fournir les produits correspon-15 dants dans lesquels est un groupe alkyle de 1 à 4 atomes de carbone.The compounds of formula (I) in which R ^ is the hydrogen atom can be alkylated in a known manner, for example by reaction of a diazoalkane of 1 to 4 carbon atoms, so as to provide the corresponding products. dants in which is an alkyl group of 1 to 4 carbon atoms.

Ce procédé de condensation des produits de formule (II) et (III) a de nombreux inconvénients : les rendements sont médiocres (par exemple on peut calculer un rendement A 20 de 27% pour l'exemple 14 de la demande de brevet européen 23392 et 9,5 % pour l'exemple 34). On pense aue c'est la présence d'accepteur d'acide qui abaisse le rendement par le fait qu'il favorise la réaction de diacylation. De plus l'utilisation d'un accepteur d'acide rend l'isolement et la 25 purification des produits finaux plus difficile et plus coûteuse.This process for condensing the products of formula (II) and (III) has many drawbacks: the yields are poor (for example, a yield A 20 of 27% can be calculated for example 14 of European patent application 23392 and 9.5% for example 34). It is thought that it is the presence of an acid acceptor which lowers the yield by the fact that it promotes the diacylation reaction. In addition, the use of an acid acceptor makes isolation and purification of the end products more difficult and more expensive.

Un but de l'invention est de remédier à ces incon-! ’ vénients.An object of the invention is to remedy these incon-! Come.

i Le procédé selon l'invention comprend la réaction 30 d'un halogènure d'acide (de préférence un chlorure, un bromure ou un iodure) avec un sulfonamide de formule (III) en l'absence d'accepteur d'acioe et à une température à laquelle l'acide halohycriaue (HCl, HBr, ΗΊ) est éliminé sous forme gazeuse du milieu réactionnel au fur et à mesure de 35 sa fcrmaticn mais sans décomposition appréciable ou proouit / de réaction de formule (I). / i/ hThe process according to the invention comprises the reaction of an acid halide (preferably a chloride, a bromide or an iodide) with a sulfonamide of formula (III) in the absence of an acio acceptor and to a temperature at which halohycriaue acid (HCl, HBr, ΗΊ) is removed in gaseous form from the reaction medium as and when it is formed but without appreciable decomposition or reaction / reaction of formula (I). / i / h

Grâce eu prccécé selon l'invention, oes rendements notablement plus élevés en cérivés sulfonamides c'acides phénoxybenzoiQues peuvent être ootenus, par exemple des rencE-ments c'au moins environ 3UL et fréouemment c'su moins 5 environ 50¾ et avec un mode ce récupération et de purification ou produit final beaucoup plus simple eue ceux des procéüés connus.Thanks to the fact that according to the invention, these significantly higher yields of sulfonamide cerides, phenoxybenzoic acids, can be provided, for example, cements at least about 3UL and frequently at least about 50¾ and with this mode. much simpler recovery and purification or final product than those of known processes.

Comme halogénure d'acice mis en oeuvre dans l'invention, on utilise en pratioue un halogénure d'acide de lu formule (II) ; ce préférence en utilise un halogénure dans la formule duquel A est le groupe N02 ou un atome de fluor, de chlore, oe brome ou d'iode ; B est un atome d'ha-loçène ; C, E et F sont l'atome d'hydrogène ; D est le groupe CF_.. On préfère également mettre en oeuvre des I -5 3 15 sulfonamioes oe formule (III) dans laauelle R est un groupe alkyle, spécialement CH^, ou un groupe CF_. f . La température à laquelle le procédé oe l'invention peut être mis en oeuvre cépeno notamment de ce que l'halo-génure d'acide de formule (II) ou le sulfonamide de formule 20 (III) sont l'un ou l'autre en large excès ou de ce aue l'on, utilise, ou non, un solvant ayant des propriétés catalytiques.As the acid halide used in the invention, an acid halide of the formula (II) is used in practice; this preference uses a halide in the formula of which A is the group NO2 or a fluorine, chlorine, oe bromine or iodine atom; B is a ha-loçene atom; C, E and F are the hydrogen atom; D is the CF_ group. It is also preferred to use sulfonamioes where formula (III) in which R is an alkyl group, especially CH 2, or a CF group. f. The temperature at which the process oe the invention can be implemented cepeno in particular that the acid halide of formula (II) or the sulfonamide of formula 20 (III) are one or the other in large excess or because of this, a solvent having catalytic properties is used or not.

Ainsi iGrsoue l'halocénure d'acice (II) est en large excès, c'est à dire que le rapport mdaire (11)/(111) 25 est compris entre environ 1,5 et 5, l'halGgénure d'acide (II) peut servir ce solvant pour la réaction et la température oe réaction peut être comprise entre 6G et 200°C, mais elle est alors oe préférence comprise entre 90 et 16GCC.Thus iGrsoue the halide of acice (II) is in large excess, that is to say that the mdaire ratio (11) / (111) 25 is between approximately 1.5 and 5, the acid halGenide ( II) can serve this solvent for the reaction and the temperature of the reaction can be between 6G and 200 ° C, but it is then preferably between 90 and 16GCC.

3u L'halocénure d'acice (II) n'ayant cas réagi peut être récupéré du milieu réactionnel par lavage avec un solvant inerte tel qu'un hydrocarbure, notamment le pentane, l'hexane, l'heptane, le cyclcpentane, le cyclohexane, le cycloneotane, le benzène, le toluène, le xylèr.e, un hydre-35 carbure halogène notamment les chlcrobenzènes, CS^, le _ / tetrahyGrofurar.ne, le dicxsnne et c'autres. /// f- 53u The halocenide of acice (II) which has not reacted can be recovered from the reaction medium by washing with an inert solvent such as a hydrocarbon, in particular pentane, hexane, heptane, cyclcpentane, cyclohexane , cycloneotane, benzene, toluene, xylèr.e, a hydrogen halide carbide including chlcrobenzènes, CS ^, _ / tetrahyGrofurar.ne, dicxsnne and others. /// f- 5

Guano on utilise un excès ce sulfonamice, c’est à aire auanc le rapport mclaire ces composés (111)/(11) est compris entre 1,5 et 5, la température réactionelle est alors généralement comprise entre 9ü et 2Q0°C et de préfé-5 rence comprise entre 140 et 160°C. En tout état de cause elle coit être au moins suffisante pour faire fondre le milieu réactionnel. L'excès ce Sulfonamide (III) peut être récupéré gu milieu réactionnel par lavage à l'eau ou un autre solvant inerte ce ce réactif (III). lu Les réactifs peuvent aussi être clssous dans un solvant inerte ayant un point c'ébullition supérieur à la température ce réaction par exemple un hydrocarbure liquide, chloré ou non tel que le benzène, le toluène, les xylènes, les mélanges oe xylènes, le cumène, auquel cas la 15 température maximale de réaction est avantageusement légèrement inférieure au point c'ébullition du solvant. Ainsi aans le cas ou cumène qui bout à environ 153°C, la réaction est mise en oeuvre ce préférence entre 13ü et 150°C. L'usage d'un solvant inerte a l'avantage pratique de permettre 20 un meilleur transfert de chaleur dans un procédé à l'échel-*, le industrielle ; il permet aussi d'éviter les surchauffes locales eu milieu réactionnel.Guano, an excess of this sulfonamice is used, it is in the air area the clear ratio of these compounds (111) / (11) is between 1.5 and 5, the reaction temperature is then generally between 9 ° and 20 ° C. and preferably between 140 and 160 ° C. In any event, it should be at least sufficient to melt the reaction medium. The excess of this sulfonamide (III) can be recovered as a reaction medium by washing with water or another inert solvent, this reagent (III). lu The reagents can also be dissolved in an inert solvent having a boiling point higher than the temperature this reaction for example a liquid hydrocarbon, chlorinated or not such as benzene, toluene, xylenes, mixtures oe xylenes, cumene , in which case the maximum reaction temperature is advantageously slightly lower than the boiling point of the solvent. Thus, in the case where cumene boils at around 153 ° C., the reaction is carried out this preference between 13 ° and 150 ° C. The use of an inert solvent has the practical advantage of allowing better heat transfer in an industrial scale process; it also makes it possible to avoid local overheating in the reaction medium.

Selon une autre variante de l'invention, on utilise , un solvant ayant une action catalytique à l'égard de la 25 réaction entre l'halogénure d'ecice (II) et le sulfonamide (III) pour fournir le phéncxybenzcylsulfonsmice (I). Le diméthylfcrmamice (=UMF ; cui bout à environ 154°C) et le diméthyiacétamioe (= DMAC ; qui oout à environ 164°C) sont particulièrement avantageux c cet écarc et leur usage per-3u met la mise en oeuvre oe température relativement basses par exemple comprises entre 6U et 12ü°C, ce préférence entre 50 et 11G°C eu encore des températures plus élevées, légèrement inférieures aux points c'ébullition de ces solvants ; la vitesse et réaction est alors plus rspice.According to another variant of the invention, use is made of a solvent having a catalytic action with regard to the reaction between the spice halide (II) and the sulfonamide (III) to provide the phencxybenzcylsulfonsmice (I). Dimethylfcrmamice (= UMF; boiled at about 154 ° C) and dimethyliacetamioe (= DMAC; which oout at about 164 ° C) are particularly advantageous c this arc and their use per-3u puts the implementation oe relatively low temperature for example between 6U and 12 ° C, this preference between 50 and 11 ° C had even higher temperatures, slightly below the boiling points of these solvents; the speed and reaction is then more efficient.

35 Les exemples suivants oennes a titre non limitatif , illustrent l'invention et rentrent comment elle neut être / i !' =: 6 1 mise en oeuvre.The following non-limiting examples illustrate the invention and show how it can be! =: 6 1 implementation.

Î Exemple IÎ Example I

Gr mélange 2 c (u, C21 rr-clt) ce méthane sulfonsmice avec 3,6 c (u,ul mole) ce chlorure ce l'acide 5- 2'-chlc- ! 5 rc-t ' - (tri f lucrométhyl ) rhéncxy -2-nitrcbenzc-ïcue. On chauffe le mélange 2U minutes à 15G°C. L'acice chlorhy- cricue se cépage eu milieu réactionnel au fur et à mesure de sa formation, ün refroidit ; en a une huile noire αυ'οπ dissout cans ce la scuce soueuse ; on filtre, acidifie le l IG filtrat à l'aide d'hCl dilué, ce qui précipite le produit :j oe formule (IV). Cn a ainsi obtenu, avec un rendement ce 71 i /6, 3,1 g oe procuit fonçant à 195-197°C et ayant une bande -1 i: ‘ d’absorption infrarouge à 1652 cm (croupe C=Q).Gr mix 2 c (u, C21 rr-clt) this methane sulfonsmice with 3.6 c (u, ul mole) this chloride this acid 5- 2'-chlc-! 5 rc-t '- (tri f lucromethyl) rhéncxy -2-nitrcbenzc-ïcue. The mixture is heated 2U minutes to 15G ° C. The hydrochloric acid grows in the reaction medium as it forms, cools; has a black oil αυ'οπ dissolved in it, the thorny flea; it is filtered, the IGI filtrate is acidified with dilute hCl, which precipitates the product: j oe formula (IV). Cn thus obtained, with a yield this 71 i / 6, 3.1 g oe proceeds darkening at 195-197 ° C and having a band -1 i: ‘of infrared absorption at 1652 cm (rump C = Q).

• Ce preauit a pour formule : :j 15• This preauit has the formula:: j 15

Cl CO-NH-SO^-CH., _ · _/ 2 3 GF γ —O— r NO„ (IV) ! \_, _ 2 t:- : 2 u p Exemple 2 f On reprocuit l'exemple I mais en utilisant 250 g oe i| chlorure c'scioe et 13G ç de méthane sulfonamide. Le pro- ! ^ cuit ce réaction est isolé directement après refroidisse- | 25 ment gu mélange par recristillisation Gans 1'iscpropancl.Cl CO-NH-SO ^ -CH., _ · _ / 2 3 GF γ —O— r NO „(IV)! \ _, _ 2 t: -: 2 u p Example 2 f We repeat Example I but using 250 g oe i | chloride c'scioe and 13G ç of methane sulfonamide. The pro- ! ^ cooked this reaction is isolated directly after cooling | 25 g mix by recrystallization Gans 1'iscpropancl.

ün a un rendement ce u 2 (165 c) en produit ce formule (IV). La structure ce ce produit est confirmée par infrarouge (bande o'abserptior à 1692 ern'^) et par résonance magnétïcue nucléaire (sirculet à 3,5 ppr? ; multiplet à c,C7 3G ppm).ün has a yield ce u 2 (165 c) produces this formula (IV). The structure of this product is confirmed by infrared (o'abserptior band at 1692 ern '^) and by nuclear magnetic resonance (sirculus at 3.5 ppr?; Multiplet at c, C7 3G ppm).

I En appiigu&nt re procédé ce l'exemple oe la cernaneeI In appiigu & nt re proceed this example o cernanee

Si ce brevet européen 23352 en utilisant la pyricine comme accepteur d'acice, r£ renrenent n'a été eue ce 25 2 / i S/If this European patent 23352 using pyricin as acice acceptor, r £ renrenent was not had this 25 2 / i S /

Claims (5)

77 5 REVChuICATIGhS i) - Procécé ce préparation ce dérivés phénoxybenzoïques à groupe sulfcnamice ce formule lü C ,B H \ / y D—/TV 0 \Λ il) / N E F 15 et ses sels, cans laquelle A est l'hyoroçène, le fluor, le chlore, le brome, l'iode, un groupe nitro; -N=NCF^ ; Pü^l-L et ses esters d'al-2G kyle de 1 à 4 atomes de carbone ; NH2, NHGH, N* ; un croupe carbGxyie ou l'un de ses cérivés fonctionnels ; un groupe mono ou dialkylamino ; un groupe NH-CO-R^ cans lequel R^ est un racical alkyle ou alkoxyle ou mcncalkyla- minc ou aialkylaminc ; un groupe alkyle ; trialkylammonio, * 25 REVChuICATIGhS i) - Carried out this preparation this phenoxybenzoic derivatives with sulfcnamice group this formula lü C, BH \ / y D— / TV 0 \ Λ il) / NEF 15 and its salts, cans of which A is hyoroçene, fluorine, chlorine, bromine, iodine, a nitro group; -N = NCF ^; Pü ^ l-L and its al-2G kyle esters of 1 to 4 carbon atoms; NH2, NHGH, N *; a carboxy rump or one of its functional cerives; a mono or dialkylamino group; an NH-CO-R ^ group in which R ^ is an alkyl or alkoxyl or mcncalkylaminc or aialkylaminc; an alkyl group; trialkylammonio, * 2 25 UHSG^R où R^ est ur. racical alkyle ou phényie ; NHüubHSG^r , cl a la signification Géjs inciouée/ alkylthic, aluyisulfinyle, aikyisuifonyle, oislkylsui- fonio, cyanosclfonyle, hycroxy, alkancyicxy, alkoxy, alkoxy suostiiué par _r. aikoyycartcr.\ le, $h, nitrcsc, -SCb·, azioe, 3>u —l\=K-P-(lwη-· ;^ , scyie ; O E est 1'hycroçènt, le fluor, le chlore, le brome, l'îcoe, ou ur croupe alkyle, sikcxy, slkyisulfinyle, ai- / kylsuïf cnyle, ,, î'.Üv, CI», Ni-,.., NhÜCn“ eu r.~ est y~,/ 55 céfini comme ci-cessus ou CONR^ ; /1/ l // / 1 >- C est i'hycrcgène eu un halogène ou un groupe al-kyle ou Gialkylaminc L· est le fluor, le chlore, le crcme, l'iooe ; ou un groupe CF,, aikyithic, slkylsulfinyle, alkylsulfonyle, Î3 rsiccencalkyie, sulfamcyie, fcrrr.yie, slkylcsrbonyle, CK ou ciméthylsmino ; E est l'nycrcçène eu un croupe halccéncai.kyie, sl- koxy, alkylsulfinyle, slkylsulfonyle, CN, CF,, Nh0, 11 % 1 CüNH^, NH-LC-k , R ayant la siçnificeticn oéjà inoi- lu quée ; F a l'une ces significations connées pour B R est un groupe -COk(RA JSCvR"5 oans lequel k est I'hycrcgène ou un croupe alkyie oe 1 à A | atorr.es oe c a roc ne j 13 h' est un groupe pr.ényie, pyridyle eu thiényle ! éventuellement substitué par un ou plusieurs atomes ti'halo- [: gène, ou groupes aiKyle, ou groupes nitre ; ou un racical I alkényle ou alkynyie ayant 1 a u atomes oe carbone ou un racical alkyie ce 1 à A atomes ce carbone éventuellement ! 2U substitué par un ou plusieurs atomes ce fluor, chlore, i brome uu ioce, ce préférence CF,, eu par un ou plusieurs j ces substituants suivants : carboxyle, alkcxycarbonyle oe 2 | à 3 atomes ce carrent, alkyicarbonyle ce 2 s 5 atomes ce j carbcne, m.onc eu cialkylcarbamoyle dans lecuel les groupes i 21 alkyie cm ce 1 à u atomes ce carbone, aikyithic, alkyisul- ! finyie, alkylsulfonyle, chacun ayant ce 1 à A atomes ce j caroone, alkylcaiccryicx\le ce 2 à 3 atomes ce carbone, | _ aikylcarbonylsmino ce 2 à 3 atomes ce carbcne, ou cyano, le : cit prccécé consistant à faire réagir un baJcgérure c'acice i 3u oe formule / I C B COM / i \ / (_/ A4 ; & / t )-û~ f—h di) (j? i 1'/ v F / j " **' j i c. ** cens iacuelle X est un atcrne ce chlore, ce brome eu c’ioce et a, Γ-, u, \j, E, F ent les significations inciouées cens la formule (1), avec un sulfcnam.ice Ge fcrrr.ule h3 SG0 {-.h (iii), r/ ayant également 1b signif icaticr-3 céjà incicuée, le Gît prccécé étant caractérise en ce que la réaction est effectuée en i'acsence c'accepteur a'acide et s une température à laquelle i'hycrscioe gazeux sous-procuit est éliminé eu milieu réactionnel au fur et à mesure ce sa formatier,, cette température étant inférieure à lu la température ce cécompositicn eu procuit ce formule (I). 2) - Procéoe selon la revencication 1 caractérisé en ce qu'en opère en présence c'un excès c'halcçénure c'acioe de formule (II). 3) - Prccécé seien le revendication 2 caractérisé en ce eue 15 le rapport molaire halcçénure c'scice Ge formule (II)/sul- fonamice ce fermuie (III) est compris entre 1,5 et 5 4) - Procédé selon l'une ces revencications 2 ou 3 caractérisé en ce eue la température réactionnelle est comprise entre 6ü et 2ûû°C, ce préférence entre Su et 16Q°C ja. 2ü 5) - Procécé' selon la revencication 1 caractérisé en ce - , au'on opère en présence c'un excès ce sulfonamioe. e) - Procécé selon la revencication 5 caractérisé en ce eue le rapport molaire sulfonamioe oe formule (III)/haicgènure , c'acioe ce formule (II) est compris entre 1,5 et 5 ^3 7) - Procécé selon l'une ces revencications 5 ou C caracté rise en ce eue la température réactionnelle est comprise entre Sü et 2U0°C, ce préférence entre iau et i£ü°C. b) - Prccécé seien ;'une ces revencicaticns 1 à 7 caractérisé en ce cLt i'cr cqère en présence c'ur solvant ayant cr ^ peint c'ébuliitiPT. supérieur à la température réactionnelle. 5) - Procécé selon la revencicaticn 6 caractérisé en ce eue le solvant est un n\ crccarcure. iu) - Prccécé sels” i£ revencication 9 caractérisé en ce que _e st-’.arc est *e cl·”tre et eue la température est cc~- J 35 prise entre et i5oDt. /y if i i i i i s i u £ 1-0 - Prccécé selon l'une ces revencicetions 1 a 8 caracté- E risé en ce eu'on opère en présence c'ur, solvant ayant aes propriétés cstalyticues ε l'éparc ce le réecticn. 12) - Prccécé selon la revencicaticn II caractérisé en ce 3 eue le solvant est le cin.éthylforrr.amice ou le diméthylacé- tamice et eue la température est comprise entre êü°C et la température c ' étulliticn eu servant. 13) - nrccécé selon la revencication 12 caractérisé en ce que la température est supérieure a fu0L. I iu 14) - Procécé selon l'une ces revencications 1 è 13 carac- I térisé en ce eue, caris les fcrrrules (I) et (II), B et X Isont l'atome ce chlore, A est l'atcme Ge chlore ou NO„. 2’25 UHSG ^ R where R ^ is ur. racical alkyl or phenyl; NHüubHSG ^ r, cl has the meaning Géjs inciouée / alkylthic, aluyisulfinyle, aikyisuifonyle, oislkylsui- fonio, cyanosclfonyle, hycroxy, alkancyicxy, alkoxy, alkoxy suostiiué by _r. aikoyycartcr. \ le, $ h, nitrcsc, -SCb ·, azioe, 3> u —l \ = KP- (lwη- ·; ^, scyie; OE is hycroçènt, fluorine, chlorine, bromine, l 'îcoe, or ur rump alkyl, sikcxy, slkyisulfinyle, ai- / kylsuïf cnyle, ,, î'.Üv, CI », Ni -, .., NhÜCn“ eu r. ~ est y ~, / 55 ceefined as ci- cessus or CONR ^; / 1 / l // / 1> - C is hydrogen in the halogen or al-kyle group or Gialkylaminc L · is fluorine, chlorine, cream, iooe; or group CF ,, aikyithic, slkylsulfinyle, alkylsulfonyle, Î3 rsiccencalkyie, sulfamcyie, fcrrr.yie, slkylcsrbonyle, CK ou ciméthylsmino; E is the anycrcene had a rump halccéncai.kyie ,, sl-koxy, alkylsulfinyl, slkyl, CN , 11% 1 CüNH ^, NH-LC-k, R having the meaning already inactive; F has one of these known meanings for BR is a group -COk (RA JSCvR "5 in which k is the hydrogen or an alkyie rump oe 1 to A | atorr.es oe ca roc ne 13 h 'is a pr.ényie group, pyridyle eu thienén! optionally substituted by a or more halo atoms: gene, or aiKyle groups, or niter groups; or a racical I alkenyl or alkynyie having 1 to u atoms oe carbon or a racical alkyie ce 1 to A atoms this carbon possibly! 2U substituted by one or more atoms ce fluorine, chlorine, i bromine uu ioce, this preference CF ,, had by one or more j these following substituents: carboxyl, alkcxycarbonyle oe 2 | to 3 atoms this carrent, alkyicarbonyle ce 2 s 5 atoms ce j carbcne, m.onc eu cialkylcarbamoyle in lecuel the groups i 21 alkyie cm ce 1 to u atoms ce carbon, aikyithic, alkyisul-! finyie, alkylsulfonyle, each having this 1 to A atoms of this carbon, alkylcaiccryicx \ ce of 2 to 3 atoms of this carbon, | _ aikylcarbonylsmino ce 2 à 3 atoms ce carbcne, ou cyano, le: cit prccécé consisting in reacting a baJgérure c'acice i 3u oe formula / ICB COM / i \ / (_ / A4; & / t) -û ~ f —H di) (j? I 1 '/ v F / j "**' ji c. ** cens iacuelle X is an atcrne this chlorine, this bromine had c'ioce and a, Γ-, u, \ j, E, F ent the meanings inciouées as the formula (1), with a sulfcnam.ice Ge fcrrr.ule h3 SG0 {-.h (iii), r / also having 1b signif icaticr-3 céjà incicée, the Gît prccécé being characterized in that the reaction is carried out in the absence of an acid acceptor and at a temperature at which the underproduced gaseous hydration is eliminated in the reaction medium as it forms, this temperature being lower than read the temperature, this cecompositicn has produced this formula (I). 2) - Process according to revencication 1, characterized in that it operates in the presence of an excess of the halcenide, this acioe of formula (II). 3) - Preceded according to claim 2 characterized in that eue 15 the molar ratio halcénure c'scice Ge formula (II) / sulfonamice this fermuie (III) is between 1.5 and 5 4) - Process according to one of these claims 2 or 3 characterized in that eue the temperature reaction is between 6 6 and 2ûû ° C, this preference between Su and 16Q ° C ja. 2ü 5) - Procécé 'according to Revencication 1 characterized in that -, au'on operates in the presence of an excess of this sulfonamioe. e) - Processed according to Revencication 5 characterized in that the molar ratio of sulfonamioe oe formula (III) / haicgenide, this acioe this formula (II) is between 1.5 and 5 ^ 3 7) - Processed according to one these claims 5 or C characterize in this eue the reaction temperature is between Sü and 2U0 ° C, this preference between iau and i £ ü ° C. b) - Prccécé seien; 'one these revencicaticns 1 to 7 characterized in this cLt i'cr cqère in the presence c'ur solvent having cr ^ painted c'ébuliitiPT. higher than the reaction temperature. 5) - Procécé according to revencicaticn 6 characterized in that eue the solvent is a n \ crccarcure. iu) - Prccécé salts ”i £ revencication 9 characterized in that _e st -’. arc is * e cl · ”tre and eue the temperature is cc ~ - J 35 taken between and i5oDt. / y if i i i i i s i u £ 1-0 - Preceded according to one of these revencicetions 1 to 8 character ized in that eu'on operates in the presence c'ur, solvent having its cstalyticues properties ε parce ce le réecticn. 12) - Prccécé according to the revencicaticn II characterized in that 3 eue the solvent is cin.éthylforrr.amice or dimethylacé-tamice and eue the temperature is between êü ° C and the temperature c 'etulliticn having servant. 13) - nrccécé according to revencication 12 characterized in that the temperature is higher than fu0L. I iu 14) - Carried out according to one of these revencications 1 to 13 characterized in this eu, because the molecules (I) and (II), B and X Is the atom this chlorine, A is the atom Ge chlorine or NO „. 2 ’ 5 L, ii, F sont l'atcme c'hycroçène, L est CF^. S 15) - Prccécé selon i'ure ces revencications 6 eu 7 carac- 15 térisé en ce eue le suifcnar.ice est tel eue h-5 est un 1 croupe slkyie ou UF_, ce préférence méthyle. Ί W O '! 16) - Procécé selon I'ure ces levencicaticns 1 à 15 carac- iij térisé en ce eue l'on effectue la réaction entre $5 L, ii, F are the hygrocene atom, L is CF ^. S 15) - Prccécé according to i'ure these revencications 6 eu 7 charac- terized in that eu suifcnar.ice is such eue h-5 is a rump slkyie or UF_, this methyl preference. Ί W O '! 16) - Processed according to these levencicaticns 1 to 15 characteristic in that the reaction between $ is carried out 1 Cl CO-C1 1 ._/ _/ Icf3 —y r o— t y N02 Dessins :.............pianenes pages dont .....Ol....... page de garde __________é.......pages de description * __________H....... pages de revendications % ________abrégé descriptif J Luxembourg, le Z6 jy|i4982 J Lem^^ataire : i' Charles München i f i* [. i1 Cl CO-C1 1 ._ / _ / Icf3 —yro— ty N02 Drawings: ............. pianenes pages of which ..... Ol ....... page of guard __________ é ....... pages of description * __________ H ....... pages of claims% ________ short description J Luxembourg, le Z6 jy | i4982 J Lem ^^ ataire: i 'Charles München ifi * [. i
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